Compounds having one or more (meth)acrylate functional groups are used in a wide variety of applications, and particularly in preparing polymers and copolymers. (Meth)acrylate functional groups include both acrylate functional groups having the structure —O—C(═O)—CH═CH2, and methacrylate functional groups having the structure —O—C(═O)—C(CH3)═CH2.
Examples of acrylates include but are not limited to alkyl acrylates such as methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate and hexadecyl acrylate; functionalized alkyl acrylates such as hydroxyethyl acrylate, hydroxypropyl acrylate, carboxyethyl acrylate, sulfopropyl acrylate, (2-(acryloyloxy)ethyl)trimethyl ammonium chloride and polyethyleneglycol acrylate. Polyacrylate materials typically are used as coatings and as additives to fluids, lubricants and surface sealants.
Examples of methacrylates include but are not limited to alkyl acrylates such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate and hexadecyl methacrylate; functionalized alkyl methacrylates such as hydroxyethyl methacrylate, hydroxypropyl methacrylate, carboxyethyl methacrylate, sulfopropyl methacrylate, (2-(methacryloyloxy)ethyl)trimethyl ammonium chloride and polyethyleneglycol methacrylate. Polymethacrylate materials typically are used as rigid plastics and as transparent glazing materials.
Acrylate and methacrylate compounds also are used as comonomers with other types of monomers in preparing copolymers. As acrylate and methacrylate monomers can undergo addition copolymerization with each other and/or with a variety of conventional alkene-functional monomers, the potential applications of (meth)acrylate compounds in polymer chemistry are numerous and diverse.
In addition, compounds having one or more (meth)acrylate functional groups also are used to form dendritic molecules. Dendritic molecules may be used as solubility enhancers, as catalyst supports, as immunoassay components, and as precursors for advanced materials. Species of the poly(amido amine) (PAMAM) class of dendrimers typically are formed by alternating reaction of ethylenediamine and methyl acrylate. Examples of PAMAM dendrimers include but are not limited to [NH2(CH2)2NH2]:(G=0); dendri PAMAM(NH2)4 and its associated higher generation molecules.
The physical and chemical properties of polymers and of dendritic molecules are affected by the chemical structures of the building blocks used to prepare the polymers and/or dendritic molecules. Alteration of the chemical structure, size and/or concentration of these building blocks can allow for modification of the properties of the polymer or dendritic molecule.
It is desirable to expand the chemical structures present in compounds having one or more (meth)acrylate functional groups, so as to expand the useful properties that can be provided by polymers or dendritic molecules formed from the compounds. With regard to polymers, for example, properties such as flexibility, toughness, etc. can be increased by incorporating chemical groups that lower the modulus or that can absorb energy, respectively. This expansion of chemical structures may be accomplished through post-polymerization processing, such as reaction with other reagents or blending with other polymers. It is especially desirable, however, to expand the chemical structures by introducing new chemical structures in the monomeric building blocks from which the polymer is formed. With regard to dendritic molecules, properties such as solubility, chemical reactivity, density, etc. can be changed by incorporating branches having different chain lengths and substitution points.
One potential approach to altering the chemical structure of compounds having one or more (meth)acrylate functional groups is to form the compounds from renewable feedstocks. Renewable feedstocks, such as fatty acids or fatty esters derived from natural oils, have opened new possibilities for the development of a variety of industrially useful substances, including specialty chemicals and intermediates. For example, renewable feedstocks can be used to prepare compounds having combinations of properties that were not available with conventional petroleum feedstocks. In another example, renewable feedstocks can be used to prepare compounds more efficiently, without requiring undesirable reagents or solvents, and/or with decreased amounts of waste or side products.
It would be desirable to provide compounds having one or more (meth)acrylate functional groups that include previously unavailable chemical structures. Preferably such compounds can be used as substitutes for conventional (meth)acrylate-functionalized compounds, while providing an increase in the renewable content of the final product formed using the compounds. Preferably such compounds can provide useful combinations of properties that are difficult to obtain using compounds formed from conventional petroleum feedstocks.